Shelter Island, NY Homes

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  $4,250,000 Pending

  • 4 Beds
  • 5 Baths
  • 3,676 Sq Ft

  8 Cove Way, Shelter Island, NY 11964

  Enviably located on Shelter Island's southern coast with 113' of waterfront on Menantic Creek, this half-acre property was fully reimagined in a high-end 2017 renovation that left no detail overlooked. Offering 3,676 +/- sq. ft. across 2 levels, the home includes 4 bedrooms, 5 baths, 2 fireplaces, a heated gunite pool, outdoor kitchen, firepit, specimen gardens, and a private deep-water dock. A

  Bridgehampton Office Saunders & Associates

  8 Cove Way, Shelter Island, NY 11964
• Explore Shelter Island

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  /25

  $30,000 per month

  • 4 Beds
  • 3 Baths
  • 2,604 Sq Ft
  • House for Rent

  4 Glynn Dr, Shelter Island, NY 11964

  This Shelter Island home is the kind of summer rental people wait all year to find-turnkey, stylish, and effortlessly comfortable. Recently renovated and designer-furnished, the home is ready for immediate enjoyment. Bright, sun-filled interiors and multiple inviting living spaces create an easy flow for summer living, whether it's slow mornings with coffee, afternoons by the pool, or relaxed

  Joseph Van Asco Douglas Elliman Real Estate

  4 Glynn Dr, Shelter Island, NY 11964
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  $975,000 Sold May 20, 2025

  1 Rebel Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,472 Sq Ft
  • Built 1981

  Last Sold Summary

  • 20% Below List Price
  • $662/SF
  • 174 Days On Market

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  1 Rebel Rd, Shelter Island, NY 11964
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  Est $1,850,000 Not Listed For Sale

  45 New York Ave, Shelter Island, NY 11964

  • 4 Beds
  • 4 Baths
  • 2,628 Sq Ft
  • Built 2005

  45 New York Ave, Shelter Island, NY 11964

  Last Sold Summary

  • $704/SF
  • 96 Days On Market

  Last Sold Price $1,850,000

  Last Listing Agent David Tenenbaum Brown Harris Stevens Hamptons
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  /41

  $2,999,000 Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2 Baths
  • 1,373 Sq Ft

  13 Tarkettle Rd, Shelter Island, NY 11964

  Nestled on a 1.08 acre lot along Shelter Island’s coveted Dickerson Creek, this Scandinavian-style waterfront cottage embodies quintessential Hamptons elegance with 100 feet of picturesque shoreline and a sparkling pool.Inside, a light-filled and inviting floor plan features three bedrooms and two newly updated bathrooms, designed for modern comfort. The stylishly renovated kitchen is sure to

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  13 Tarkettle Rd, Shelter Island, NY 11964
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  /14

  $8,700 per month

  • 4 Beds
  • 3 Baths
  • 2,018 Sq Ft
  • House for Rent

  59 Peconic Ave, Shelter Island, NY 11964

  Classic Cape Cod Retreat Near Shell BeachEnjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 3-bath home is set in a friendly, sought-after summer community.The bright, open living and dining area

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  59 Peconic Ave, Shelter Island, NY 11964
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  $2,679,000 Sold Jan 21, 2026

  156 Ram Island Dr, Shelter Island, NY 11964

  • 4 Beds
  • 4 Baths
  • 3,420 Sq Ft
  • Built 1995

  Last Sold Summary

  • 36% Below List Price
  • $783/SF
  • 446 Days On Market

  Current Estimated Value $3,116,196

  Last Listing Agent Mary Elizabeth Galle Corcoran

  156 Ram Island Dr, Shelter Island, NY 11964
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  Est $1,636,515 Not Listed For Sale

  16 Great Circle Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,637 Sq Ft
  • Built 1985

  16 Great Circle Dr, Shelter Island, NY 11964

  Last Sold Summary

  • 4% Above List Price
  • $965/SF
  • 390 Days On Market

  Last Sold Price $1,579,000

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sotheby's
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  /20

  $2,675,000

  • 4 Beds
  • 3 Baths

  55 Peconic Ave, Shelter Island, NY 11964

  Welcome to 55 Peconic Avenue, a bold, newly built statement home completed in 2022 and set on an expansive 1.4-acre parcel in one of Shelter Island's most coveted locations. Designed for true year-round living, this residence captures southwest-facing water views, dramatic light, and a seamless indoor-outdoor lifestyle that today's buyers demand. The main level delivers a clean, open-concept

  Jack Richardson SERHANT.

  55 Peconic Ave, Shelter Island, NY 11964
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  /35

  $50,000 per month

  • 4 Beds
  • 3.5 Baths
  • 3,800 Sq Ft
  • House for Rent

  47L S Ferry Rd, Shelter Island, NY 11964

  Rental is Available in 2026: June $40,000 July $50,000., Aug. $60,000. Sept. $40,000. Located in our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities,

  Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  47L S Ferry Rd, Shelter Island, NY 11964
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  $795,000 Sold Oct 10, 2025

  33B S Midway Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • Built 1950

  Last Sold Summary

  • 11% Below List Price
  • 142 Days On Market

  Current Estimated Value $1,069,908

  Last Listing Agent Shane Donahue The Agency Hamptons

  33B S Midway Rd, Shelter Island, NY 11964
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  Est $2,933,160 Not Listed For Sale

  3 Sea Gull Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,650 Sq Ft
  • Built 1953

  3 Sea Gull Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 50% Above List Price
  • $1,182/SF
  • 322 Days On Market

  Last Sold Price $1,950,000

  Last Listing Agent Cynthia Barrett Brown Harris Stevens Hamptons
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  /30

  $2,950,000 Open Sat 1:30PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  12 Terry Dr, Shelter Island, NY 11964

  Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach.Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  12 Terry Dr, Shelter Island, NY 11964
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  /26

  $14,400 per month

  • 4 Beds
  • 2 Baths
  • 2,669 Sq Ft
  • Property for Rent

  12 Dogwood Ln, Shelter Island, NY 11964

  Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect

  Mackenzie Needham Daniel Gale Sothebys Intl Rlty

  12 Dogwood Ln, Shelter Island, NY 11964
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  $2,650,000 Sold Oct 16, 2025

  7 Gazon Rd, Shelter Island, NY 11964

  • 3 Beds
  • 2.5 Baths
  • 1,901 Sq Ft
  • Built 1955

  Last Sold Summary

  • 8% Below List Price
  • $1,394/SF
  • 130 Days On Market

  Current Estimated Value $2,711,082

  Last Listing Agent Terry Thompson Douglas Elliman Real Estate

  7 Gazon Rd, Shelter Island, NY 11964
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  Est $2,185,000 Not Listed For Sale

  6 Behringer Ln, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft
  • Built 2023

  6 Behringer Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 1% Below List Price
  • $638/SF
  • 263 Days On Market

  Last Sold Price $2,200,000

  Last Listing Agent Sheri Winter Parker Corcoran
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  $3,499,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,856 Sq Ft

  9 Locust Woods Dr, Shelter Island, NY 11964

  Welcome to Shelter Island — a place where time slows down and nature takes center stage. Accessible only by ferry, this rare island community offers a level of peace, privacy, and authenticity that is nearly impossible to find in today’s world. Set on over 2 acres of beautifully engineered rolling landscape, this property has been thoughtfully designed to enhance natural beauty while addressing

  Ron Moschetta Keller Williams Realty Greater

  9 Locust Woods Dr, Shelter Island, NY 11964
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  $7,500 per month

  • 4 Beds
  • 2.5 Baths
  • 2,825 Sq Ft
  • House for Rent

  42 N Menantic Rd, Shelter Island, NY 11964

  Escape to Tranquility Base, a light-filled modern retreat where timeless mid-century style meets today’s elevated comforts. Thoughtfully renovated and expanded, this 4-bedroom, 2.5-bath home is surrounded by lush, landscaped grounds and designed for seamless indoor–outdoor living—thanks to five sliding glass doors that open to a heated gunite pool and expansive entertaining deck.Enjoy the

  Jeanmarie Bay William Raveis New York LLC

  42 N Menantic Rd, Shelter Island, NY 11964
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  $1,450,000 Sold May 30, 2025

  5 Wade Rd, Shelter Island, NY 11964

  • 3 Beds
  • 3 Baths
  • 1,854 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Below List Price
  • $782/SF
  • 20 Days On Market

  Current Estimated Value $1,435,729

  Last Listing Agent Rosanna Piazza Signature Premier Properties

  5 Wade Rd, Shelter Island, NY 11964
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  Est $2,105,899 Not Listed For Sale

  Unlisted Address

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft
  • Built 1954

  Unlisted Address

  Last Sold Summary

  • 25% Below List Price
  • $1,284/SF
  • 39 Days On Market

  Last Sold Price $2,825,000

  Last Listing Agent Susan Cincotta Susan C Cincotta
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  /15

  $3,850,000

  • 4 Beds
  • 5.5 Baths
  • 3,985 Sq Ft

  8 Hilo Dr, Shelter Island, NY 11964

  This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail,

  Enzo Morabito Douglas Elliman Real Estate

  8 Hilo Dr, Shelter Island, NY 11964
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  /18

  $63,000 per month

  • 3 Beds
  • 2 Baths
  • 1,487 Sq Ft
  • House for Rent

  4 Ivy Place, Shelter Island, NY 11964

  Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of for overflow guests.

  Sheri Winter Parker Corcoran

  4 Ivy Place, Shelter Island, NY 11964
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  $4,350,000 Sold Oct 31, 2025

  7 Westmoreland Dr, Shelter Island, NY 11964

  • 6 Beds
  • 4.5 Baths
  • 4,957 Sq Ft
  • Built 1901

  Last Sold Summary

  • 1% Above List Price
  • $878/SF
  • 18 Days On Market

  Last Listing Agent Carl Gambino Compass Greater NY LLC

  7 Westmoreland Dr, Shelter Island, NY 11964
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  Est $1,265,918 Not Listed For Sale

  105 S Ferry Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2.5 Baths
  • 1,726 Sq Ft
  • Built 1977

  105 S Ferry Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 40% Above List Price
  • $523/SF
  • 177 Days On Market

  Last Sold Price $902,500

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
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  /46

  $3,395,000 Open Sat 1PM - 2:30PM

  • 4 Beds
  • 3 Baths
  • 2,200 Sq Ft

  52 S Midway Rd, Shelter Island, NY 11964

  Around the bend from Turkem's Rest and a short paddle from Salt and Shipwreck, this recently renovated, 4-bedroom, circa 1908 Shelter Island farmhouse, on a shy acre, is perched above Menantic Creek with a substantial dock and profits from panoramic water views with southwestern exposure for magical sunsets. Wide waterfront vistas unfold across beautiful landscaping by Marders, broad greens lined

  Shane Donahue The Agency Hamptons

  52 S Midway Rd, Shelter Island, NY 11964
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  /35

  $75,000 per month

  • 6 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • House for Rent

  15 Montclair Ave, Shelter Island, NY 11964

  Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

  Margot Reutter Corcoran

  15 Montclair Ave, Shelter Island, NY 11964
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  $4,950,000 Sold May 30, 2025

  104 S Ferry Rd, Shelter Island, NY 11964

  • 5 Beds
  • 5.5 Baths
  • 4,040 Sq Ft
  • Built 2023

  Last Sold Summary

  • $1,225/SF
  • 14 Days On Market

  Current Estimated Value $4,838,133

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  104 S Ferry Rd, Shelter Island, NY 11964
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  Not Listed For Sale

  8 Crescent Way, Shelter Island, NY 11964

  • 4 Beds
  • 3.5 Baths
  • 2,800 Sq Ft
  • Built 2017

  8 Crescent Way, Shelter Island, NY 11964

  Last Sold Summary

  • $898/SF
  • 96 Days On Market

  Last Sold Price $2,515,000

  Last Listing Agent Christine Beckwith Douglas Elliman Real Estate
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  $4,445,000

  • 6 Beds
  • 8 Baths
  • 5,622 Sq Ft

  100 S Ferry Rd, Shelter Island, NY 11964

  A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep.Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style

  Christine Beckwith Douglas Elliman Real Estate

  100 S Ferry Rd, Shelter Island, NY 11964
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  $5,700,000 Sold Apr 07, 2026

  21 Thompson Rd, Shelter Island, NY 11964

  • 2 Beds
  • 2 Baths
  • 1,504 Sq Ft
  • Built 2022

  Last Sold Summary

  • 16% Below List Price
  • $3,790/SF
  • 115 Days On Market

  Current Estimated Value $5,621,055

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  21 Thompson Rd, Shelter Island, NY 11964
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  Not Listed For Sale

  79A N Midway Rd, Shelter Island, NY 11964

  • 4 Beds
  • 2.5 Baths
  • 1,794 Sq Ft
  • Built 1979

  79A N Midway Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 17% Above List Price
  • $690/SF
  • 81 Days On Market

  Last Sold Price $1,237,500

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sotheby's
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  /35

  $2,485,000 Open Sat 11AM - 12:30PM

  • 6 Beds
  • 4 Baths
  • 3,413 Sq Ft

  14 Freds Ln, Shelter Island, NY 11964

  Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with

  Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

  14 Freds Ln, Shelter Island, NY 11964
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  $660,000 Sold Dec 02, 2025

  8 Wheeler Rd, Shelter Island, NY 11964

  • Land
  • 1.2 Acres
  • $550,000 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 99 Days On Market

  Last Listing Agent Nicholas Planamento William Raveis New York LLC

  8 Wheeler Rd, Shelter Island, NY 11964
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  Est $734,322 Not Listed For Sale

  3 N Cartwright Rd, Shelter Island, NY 11964

  3 N Cartwright Rd, Shelter Island, NY 11964

  Last Sold Summary

  • 3% Above List Price
  • 39 Days On Market

  Last Sold Price $710,000

  Last Listing Agent Scott Bennett Douglas Elliman Real Estate
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  $1,035,000 Pending

  • 3 Beds
  • 2 Baths

  26 Ole Buck Run, Shelter Island, NY 11964

  ***NEW PRICE*** This recently renovated 3 bedroom, 2 bath home with wood burning fireplace is situated on .89 private acres. The home now has a: new roof, siding, and air conditioners. Newly refinished floors and painted interior. New back decks and exterior basement entry. Full basement with a walkout makes for a possible fourth ensuite bedroom. Adjacent to the 14 acre Westmoreland Farm Open

  Angelo Piccozzi DERING HARBOR REAL ESTATE LLC

  26 Ole Buck Run, Shelter Island, NY 11964
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  $1,180,000 Sold Mar 26, 2026

  1 Gazon Rd, Shelter Island, NY 11964

  • 4 Beds
  • 3 Baths
  • 2,618 Sq Ft
  • Built 1962

  Last Sold Summary

  • 13% Below List Price
  • $451/SF
  • 151 Days On Market

  Current Estimated Value $1,270,036

  Last Listing Agent Kristy Naddell Douglas Elliman Real Estate

  1 Gazon Rd, Shelter Island, NY 11964
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  Est $1,457,494 Not Listed For Sale

  1 Deer Park Ln, Shelter Island, NY 11964

  • 3 Beds
  • 3.5 Baths
  • 2,460 Sq Ft
  • Built 1993

  1 Deer Park Ln, Shelter Island, NY 11964

  Last Sold Summary

  • 39% Above List Price
  • $427/SF
  • 153 Days On Market

  Last Sold Price $1,050,000

  Last Listing Agent Debra Von Brook Binder Daniel Gale Sotheby's
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  $1,375,000

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  20 Crescent Way, Shelter Island, NY 11964

  This lovely home is nicely sited ona shy acre close to Menhaden LaneBeach and Golf. Hard wood floors throughout.Spaciousliving room with cathedral ceiling, fireplace andsliders which open onto a large deck and yard beyond. Three nice sized bedrooms, two full baths, formal dining room, chef's kitchen with gas stove, Den/potential media roomwith egress, two-car garage+.Yard is fenced with plenty of

  Melina Wein M WEIN REALTY INC

  20 Crescent Way, Shelter Island, NY 11964
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  $1,725,000 Sold Jan 14, 2026

  27 Country Club Dr, Shelter Island, NY 11964

  • 3 Beds
  • 2 Baths
  • 3,170 Sq Ft
  • Built 2011

  Last Sold Summary

  • 13% Below List Price
  • $544/SF
  • 221 Days On Market

  Current Estimated Value $2,086,370

  Last Listing Agent Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

  27 Country Club Dr, Shelter Island, NY 11964
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  Not Listed For Sale

  18 Dickerson Dr, Shelter Island, NY 11786

  • 4 Beds
  • 3.5 Baths
  • 2,774 Sq Ft
  • Built 1973

  18 Dickerson Dr, Shelter Island, NY 11786

  Last Sold Summary

  • $901/SF
  • 16 Days On Market

  Last Sold Price $2,500,000

  Last Listing Agent Michael Brennan Douglas Elliman Real Estate

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